


Dean Plays Dress Up

by AeonFlux40



Category: Supernatural
Genre: Bottom Dean, Dress Up, Gay Sex, M/M, Roleplay, Top Sam, Wincest - Freeform
Language: English
Status: Completed
Published: 2017-02-23
Updated: 2017-02-23
Packaged: 2018-09-26 12:30:34
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,161
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9896564
Author URL: https://archiveofourown.org/users/AeonFlux40/pseuds/AeonFlux40
Summary: Sam comes home with a gift for Dean.





	

“What’s this?” Dean asked as Sam placed the package on the dining room table. Sam stood behind Dean and put his arms around his waist, nuzzling his neck softly.

“Open it.“

Dean opened the package and his eyes went wide. ”Sam? What-?” he turned around, holding up the outfit that Sam had picked out for him.

“Do you like it?” Sam asked.

“I don’t…I don’t know what to say.” Dean replied.

“Go try it on. I want to see how it fits.”

”But-”

Sam gripped Dean’s chin and kissed him. “Don’t argue. Just do it.”  
  
Dean grabbed everything and headed into the bedroom. He looked over everything as he laid it all out on the bed. It was a French maid’s outfit. Sam had bought him a French maid’s outfit. The top had short sleeves and corset lace up in the back, bottom was skirt/petticoat-white lacy panties, a silky choker, and a garter for his leg. Dean sighed. He was always one to indulge Sam in his fantasies, but this…..  
  
He picked up the panties and held them in his hands. Dean preferred silk, but he liked lace too. _Might not be so bad. _he thought. Dean stripped down and put on the panties. He groaned at the feel of them on his ass, his dick getting hard. They were a bit snug, but felt really good. The skirt was next. That went on fairly easy. The top, however, was a totally different story.__

Dean poked his head out of the bedroom. “Sam? Uh…I need…I need some help in here. Please.“

Sam walked down the hallway toward the bedroom. ”Dean, what- _wow _.” Sam stopped dead in his tracks as soon as he saw Dean. He exhaled slowly.__

“This top…it’s more like a corset because of this stupid lace up in the back. How am I supposed to get this on by myself?” Sam was quiet. Dean had his back to him, showing the lace up he was struggling with. Sam just stood there, taking it all in.

_God bless those muscles. ___  
  
“Well, are you gonna help me with this thing or not?” Dean asked.  
  
“Not.” Sam replied.  
  
Sam walked up behind Dean and shoved the top down onto the floor. He reached up under the front of the skirt and rubbed Dean’s muscular thighs. Dean groaned and leaned back against Sam. “So fucking hot,” Sam whispered. “I can’t keep my hands off.” Dean arched his back, rubbing his ass up against Sam. Dean’s dick was leaking into the panties. Sam pulled himself away from Dean just enough to slap his ass hard. Dean moaned. “You like that, baby?” Sam asked. Dean whimpered. Sam reached up and grabbed Dean’s hair, pulling his head back. “I _asked _you a question.“ Sam said.__

“Yes.“ Dean swallowed loudly. ”Yes, I like it.“  
  
”Good boy.“  
  
Sam shoved Dean onto the bed and got on his knees behind him. He caressed Dean’s lace covered ass with his hands. “These panties look great on you.“

”Yeah? You think so?“ Dean wiggled his butt in the air.

”I know you like silk,“ Sam said, ”but the lace kind of completed the outfit better. At least, _I _thought so.“ Sam chuckled. He slid the panties down just enough to expose Dean’s pink ass, but keeping his hard cock restrained in the front. He leaned over, gently kissed Dean’s ass, then gave it another hard slap. Dean grunted. Sam spanked him a few more times, just enough to make the skin on Dean’s ass hot and red. Sam spread Dean’s ass cheeks and went straight to his tight hole with his tongue. Dean gasped loudly and gripped the bed sheets.__

“Damn, baby boy. Fuck.“ he panted. Dean tried to push himself more against Sam’s face, but Sam held his hips in place.

”Be still, big brother.” Sam said. ”I’ll take care of you. Don’t I always take care of you?“

”Yes.“ Dean whimpered in response.  
  
”Good boy.”  
  
Sam could feel Dean’s legs starting to shake as he held them in place, working his tongue in and around his hole.

“Please, Sammy. _Please _.” Dean begged, trying to push himself further against Sam’s face.__

“Hold _still _.” Sam said, slapping Dean’s ass hard. “You’re gonna take what I give you, got that?”__

Dean whimpered and nodded. Sam chuckled. He spread Dean’s ass cheeks wide and thrust his tongue inside. Dean gasped and whined. The feeling was almost too much for him.

“Sammy, I-…I don’t know how much longer I can hold out.”

Sam stopped. “Well, we can’t have you coming too soon, now can we?” Dean groaned in response. Sam chuckled. “On your back. _Now _.” Dean complied and rolled over to face Sam. Dean took the panties off and threw them to the side. Sam reached up and caressed Dean’s face. “You’re so beautiful like this, big brother.” Dean blushed.__

“Sam, stop it.”

“What’s the matter? You don’t like it when I call you beautiful?”

“I’m not a girl.”

“You don’t have to be a girl to be beautiful, Dean.” Sam said. He leaned over and kissed Dean gently on the lips. “I love you.”

“I love you too, Sammy.”

Dean gasped as Sam gently entered him. Eyes half open, lips parted, damn he really was beautiful. Sam lifted Dean’s legs up and thrust deeper into him. It was slow and tortuous, just the way Sam knew Dean liked it but would never admit. Sam savored every gasp, every whimper, every sound that came out of his brother’s mouth.

“Sam, _please _.” Dean begged. He grabbed onto Sam’s waist, trying to get him to go faster, but Sam wouldn’t. Sam reached down and gently stroked Dean’s hard cock. He loved taking his brother apart like this. It was definitely one of his favorite things. Sure, Sam liked to fuck Dean hard and fast too, but this….this was different.__

“God, Dean, you feel so good.”

Sam leaned over and kissed Dean, gently biting his lower lip. Dean grabbed onto Sam’s shoulders and pulled him close, claiming Sam’s mouth with his own. “So needy.” Sam whispered against Dean’s lips. Sam pushed Dean’s legs up so that his knees were almost to his chest. He thrust deeper, and hit that sweet spot that made Dean cry out.

“Is that it, big brother? I’m gonna keep hitting it until you come, Dean.”

Dean couldn’t respond with words. Dean couldn’t say much of _anything _at this point, just moaning Sam’s name over and over every time Sam thrust into him deeper and deeper.__

__“That’s it, Dean. Say my name. _Scream _it.”___ _

____Sam picked up the pace, and started fucking into Dean hard. He wasn’t going to last much longer. Sam reached down and stroked Dean’s hard cock._ _ _ _

____“Come for me, Dean.”_ _ _ _

____Dean came with a shout, spilling all over his new skirt. Sam came shortly after, panting heavily and sweating._ _ _ _

____“Jesus, Sam. I love you so much.”_ _ _ _

____“I love you too, big brother.”_ _ _ _


End file.
